Fragmentation pathways of heroin‐related alkaloids revealed by ion trap and quadrupole time‐of‐flight tandem mass spectrometry

Zhang, Zhengxiang; Yan, Bo; Liu, Kelin; Bo, Tao; Liao, Yiping; Liu, Huwei

doi:10.1002/rcm.3686

Cited by 33 publications

(35 citation statements)

References 27 publications

(35 reference statements)

Supporting

Mentioning

Contrasting

Order By: Relevance

“…SI 2) to get more insight in the proposed fragmentation route of opiates. Fragmentation pathways at the high end of the spectra have been studied by other authors, and our accurate‐mass data confirm the earlier interpretation. However, fragment ions at the lower end of the spectra have generally been ignored.…”

Section: Resultssupporting

confidence: 90%

“…This demonstrates that D‐labeling of heroin and related compounds was important in elucidation of the fragmentation pathway. From our point of view, the structure suggested by others for the fragment ion m/z 181 of heroin and related compounds, with a 4‐hydroxy group, is unlikely . We think that the 3‐hydroxy group is more appropriate (Fig.…”

Section: Resultsmentioning

confidence: 79%

“…The most abundant fragment results from the loss of H 3 C–CH 2 = N–CH 3 (57 Da) to fragment ion with m/z 211 (C 14 H 11 O 2 + ), although fragment ions due to the loss of H 2 C = N–CH 3 (43 Da) to m/z 225 (C 15 H 13 O 2 + ) and H 2 N–CH 3 (31 Da) to m/z 237 (C 16 H 13 O 2 + ) are also observed. The structure proposed by Zhang et al . for the ion with m/z 225, involving a seven‐member ring, seems unlikely, as it would require significant rearrangement of the structure; an alternative proposal is given in Fig.…”

Section: Resultsmentioning

confidence: 99%

See 2 more Smart Citations

Fragmentation pathways of drugs of abuse and their metabolites based on QTOF MS/MS and MSE accurate-mass spectra

et al. 2011

View full text Add to dashboard Cite

15A study of the fragmentation pathways of several classes of drugs of abuse (cannabinoids, ketamine, amphetamine and amphetamine-type stimulants, cocaine and opiates) and their related substances has been made. The knowledge of the fragmentation is highly useful for specific fragment selection or for recognition of related compounds when developing MS-based analytical methods for the trace level 20 determination of these compounds in complex matrices. In this work, accurate-mass spectra of selected compounds were obtained using liquid chromatography coupled to quadrupole time-of-flight mass spectrometry, performing both MS/MS and MS E experiments. As regards fragmentation behavior, the mass spectra of both approaches were quite similar, and were useful to study the fragmentation of the drugs investigated. 25Accurate-mass spectra of 37 drugs of abuse and related compounds, including metabolites and deuterated analogues, were studied in this work and structures of fragment ions were proposed. The accurate-mass data obtained allowed to confirm structures and fragmentation pathways previously proposed based on nominal mass measurements, although new insights and structure proposals were achieved in some 30 particular cases, especially for amphetamine and amphetamine-type stimulants, 11-nor-9-carboxy-∆ 9 -tetrahydrocannabinol (THC-COOH) and opiates. KEYWORDSIllicit drugs of abuse, fragmentation pathways, metabolites, accurate mass, liquid 35 chromatography, time-of-flight mass spectrometry

show abstract

Section: Resultssupporting

confidence: 90%

Section: Resultsmentioning

confidence: 79%

Section: Resultsmentioning

confidence: 99%

See 1 more Smart Citation

Fragmentation pathways of drugs of abuse and their metabolites based on QTOF MS/MS and MSE accurate-mass spectra

et al. 2011

View full text Add to dashboard Cite

show abstract

“…Further elimination of methyl and methoxy radicals gave the biradical ions at m/z 251 for both by-products. Same fragmentaBrought to you by | New York University Bobst Library Technical Services Authenticated Download Date | 6/1/15 1:31 PM tions were observed for protonated acetylcodeine and thebaine [22].…”

Section: Tandem Mass Spectrometrymentioning

confidence: 71%

Degradation of morphine and codeine by gamma radiation in methanol solution

Kantoğlu

Ergün

2014

Radiochimica Acta

View full text Add to dashboard Cite

The high concentrations of opiate and solvent in wastewater are toxic to biological life and affect the aquatic environment. Therefore, it must be treated by an advanced treatment process such as ionizing radiation. Effect of organic media on morphine and codeine during gamma irradiation was determined for the first time in this paper. Samples were irradiated at ambient temperature and in air environment at various doses (0, 10, 20, 30, 40, 50 and 60 kGy). Gamma irradiation-induced changes in the molecular structure of morphine and codeine were monitored by direct infusion electrospray ionization mass spectrometry in positive ion mode. The mass of the byproducts were appeared to be more than the mass of the original alkaloids. Molecular structures of the by-products and reaction pathways were proposed. Oxygenated morphine and oxygenated codeine were identified in the presence of oxygen. However, solvent radical addition reactions were observed as the main mechanism for the byproduct formation in oxygen-free irradiation. The results indicated that 89% of morphine and 98% of codeine were degraded at dose of 50 kGy. In addition, alkaloids and their by-products were not detected above 50 kGy.Here, we demonstrated that ionizing radiation process is a promising method to remove morphine and codeine in solvent/opiate rich industrial wastewater.

show abstract

“…Rinehart 1967) as well as ESI-MS tandem ionization of morphine (Raith et al 2003) or CID ionization of morphine (Zhang et al 2008). The MS 3 spectra of all components of the cocaine sample were measured; as an example, the spectrum of cocaine is given in Fig.…”

mentioning

confidence: 99%

HPLC/MS Analysis of Historical Pharmaceutical Preparations of Heroin and Cocaine

2010

View full text Add to dashboard Cite

Pharmaceutical preparations of heroin and cocaine more than seventy years old were analyzed using RP-HPLC. The composition of mobile phase was optimized. The components were identified by MS 2 or MS 3 , and the APPI fragmentation mechanisms of compounds found were proposed. The sample of heroin hydrochloride injection solution consists of 96.1% morphine and 3.9% of codeine. The sample of cocaine hydrochloride injection solution consists of 26.9% cocaine, 31.5% benzoylecgonine, 17.4% ecgonine, and 24.2% ecgonine methyl ester.

show abstract

Fragmentation pathways of heroin‐related alkaloids revealed by ion trap and quadrupole time‐of‐flight tandem mass spectrometry

Cited by 33 publications

References 27 publications

Fragmentation pathways of drugs of abuse and their metabolites based on QTOF MS/MS and MSE accurate-mass spectra

Fragmentation pathways of drugs of abuse and their metabolites based on QTOF MS/MS and MSE accurate-mass spectra

Degradation of morphine and codeine by gamma radiation in methanol solution

HPLC/MS Analysis of Historical Pharmaceutical Preparations of Heroin and Cocaine

Contact Info

Product

Resources

About